Iodine → HCID 86658564, compound

Participants

Reaction Conditions

Reaction Steps

According to Scheme 9 Step 3: To a solution of 1-(4-methylpyrimidin-2-yl)thiourea (0.79 mmol, 133 mg) in pyridine (1 mL) was added iodine (0.79 mmol, 200 mg). The solution was stirred at 80° C. for 15 minutes and then 3,3,3-trifluoro-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)propan-1-one (0.79 mmol, 235 mg) was added. The reaction mixture was stirred for 2 hours at 80° C. The solvent was removed under reduced pressure. The crude mixture was partitioned between AcOEt and a saturated aqueous solution of Na2CO3. The aqueous layer was extracted with AcOEt. The combined organic layers were dried over MgSO4, were filtered and were evaporated under reduced pressure. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (99:1) to afford 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-N-(4-methylpyrimidin-2-yl)-5-(trifluoromethyl)thiazol-2-amine (0.40 mmol, 180 mg, 51%).

Provenance & Evidence